AN UNPRECEDENTED ELECTRONIC PREFERENCE FOR THE META PRODUCT IN DIELS-ALDER REACTIONS OF ETHYNYLDIALKYLBORANES - [(TRIMETHYLSILYL)ETHYNYL]-9-BBN AS A REACTIVE AND VERSATILE DIENOPHILE Academic Article uri icon

abstract

  • [(Trimethylsilyl)ethynyl]-9-BBN undergoes DielsAlder reactions with acyclic dienes at 100 C to afford 1,4-cyclohexadienes in high yields. The novel regiochemistry of these reactions is consistent with an ab initio prediction of advanced bonding to boron in a [4 atom + 3 atom] transition state. 1992, American Chemical Society. All rights reserved.

published proceedings

  • JOURNAL OF ORGANIC CHEMISTRY

altmetric score

  • 0.25

author list (cited authors)

  • SINGLETON, D. A., & LEUNG, S. W.

citation count

  • 44

complete list of authors

  • SINGLETON, DA||LEUNG, SW

publication date

  • January 1992